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Born in Fairfax, Virginia to mother, Tammy Hill, Dawkins was raised by Andre and Pamela Dawkins. He started his high school basketball career at Deep Creek High School in Chesapeake, Virginia, before transferring to Atlantic Shores Christian School, where he reclassified as a freshman. He was a three-time first team all-state, all-conference, and all-state tournament team selection. He was named conference player of the year as a sophomore, after averaging 22.4 points and 7.0 rebounds per game.[1]

In December 2009 an automobile accident in West Virginia killed Dawkins' sister, Lacey, and injured their mother, Tamara Hill. The two had been on their way from Columbus, Ohio, to see Dawkins play against St. John's.[3] He played in 38 games in the 2009–10 season, averaging 12.6 minutes and 4.4 points per game.[4]

As a freshman he was a back-up guard on Duke's 2010 national champion team. In the NCAA tournament Elite Eight game (March 28, 2010) against Baylor, Dawkins hit two crucial three-pointers in the first half to help Duke stay in the game.

In the Summer of 2012, Duke announced that Dawkins would redshirt the 2012–13 season.[5]

On April 11, 2013, Dawkins announced he was returning to Duke for his Senior season and changing his number from 20 to 34 (a nod to one of his idols, Ray Allen, who changed his number from 20 to 34 for the final stage of his career when he joined the Miami Heat).[6]

On January 23, 2015, Dawkins signed a 10-day contract with the Boston Celtics, but was immediately assigned to their D-League affiliate, the Maine Red Claws.[13] He was recalled on the afternoon of January 29, but was reassigned to Maine later that day after one practice with the Celtics.[14] On February 1, he was recalled again by the Celtics to suit up for their home game against his former team, the Miami Heat.[15] The next day, he signed a second 10-day contract with the Celtics.[16] On February 5, he was reassigned to Maine,[17] only to be recalled again five days later.[18] Following the expiration of his second 10-day contract on February 12, he parted ways with the Celtics before appearing in a game for them. Two days later, he returned to the Sioux Falls Skyforce.[19]